Exchange Server

Steve Manatt · Guest

I have several web applications that send e-mail to users and internal
mailboxes based on what happens. I have setup the SMTP service on IIS
(Server 2003 SP1) to use our Exchange server as a Smart Host by IP address
[192.168.168.13]. We do this for 2 reasons:

1. To get the correct IP address in the message header for spam filtering
reasons.
2. To be able to successfully get messages to internal users - if left to
it's own devices, the IIS SMTP server would resolve the internal domain as a
public address and try to send it out the firewall, not to the Exchange
Server.

Up until around the time of SP2 for Exchange was applied, everything worked
great. Mail flowed just fine from internal web servers. Now all messages
generated via my applications are stuck in the IIS SMTP Queue folder and
Event Viewer has an error:

Source: smtpsvc
ID: 4006

Message delivery to the host '192.168.168.13' failed while delivering to the
remote domain 'fbclr.org' for the following reason: The connection was
dropped by the remote host.

fbclr.org is our domain, but it could be any domain in that message. From
the Exchange Server's standpoint, there are several "Connections" listed from
the IIS Server under the SMTP Protocol that stay and eventually time out.
All servers spoken up to this point are part of the AD Domain "fbclr.local"
and are all on the same IP network.

There are two strange behaviors that are confounding the process.

1. I can send messages using the same ASP applications from our Public
webserver, which is not part of the AD Domain. Everything else is identical
on this server as the other IIS Servers in terms of SMTP settings.
2. If I restart (OS Restart, not service restart) the web server that has
the mail backed up, the messages will actually be delivered during the
shutdown process. This has been a replicated behavior on one other Windows
2000 server and my XP Pro workstation.

I guess I have two questions:

1. Is there something in SP2 that is causing the messages to not flow? If
so, how might "exceptions" be applied to the new security measures to allow
specific servers to "relay" through the server?
2. Is there a "proper" configuration for IIS 6.0 to make this process work?

Thanks for your help - I have been trying to solve this for a week now.

Steve Manatt · Guest

The solution ended up being to put the IP address of the IIS Server in it's
SMTP Server's list of allowed Relay hosts. Why, I don't know why - perhaps
one of you smartheads will know why.

Just so it is clear what I did:

The IIS Server that hosts the ASP code has an IP address of 192.168.168.25.

1. I went to the IIS Admin MMC, went to the SMTP Server properties ~ Access
~ Relay
2. I chose "Only the list below" and added 19.168.168.25 to the list
3. I left the bottom checkbox checked that talks about authenticated users
4. Hit OK and mail immediately was delivered

"Steve Manatt" wrote:

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